This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
E5531
Accession Number
DB06447
Type
Small Molecule
Groups
Investigational
Description

E5531 is an endotoxin antagonist.

Structure
Thumb
Synonyms
Not Available
External IDs
E 5531 / E-5531 / E5531
Categories
UNII
4468VT5E70
CAS number
162679-36-9
Weight
Average: 1455.831
Monoisotopic: 1454.905998023
Chemical Formula
C73H136N2O22P2
InChI Key
GDODKYPBSZCPOO-XFMGTHRKSA-N
InChI
InChI=1S/C73H136N2O22P2/c1-7-12-17-22-25-28-31-36-40-45-58(77)53-63(79)74-66-70(90-51-49-57(76)44-39-34-20-15-10-4)68(82)61(94-73(66)97-99(86,87)88)56-92-72-67(75-64(80)54-59(78)46-41-37-32-29-26-23-18-13-8-2)71(69(96-98(83,84)85)62(95-72)55-89-6)91-52-50-60(47-42-35-21-16-11-5)93-65(81)48-43-38-33-30-27-24-19-14-9-3/h30,33,57,60-62,66-73,76,82H,7-29,31-32,34-56H2,1-6H3,(H,74,79)(H,75,80)(H2,83,84,85)(H2,86,87,88)/b33-30-/t57-,60-,61-,62-,66-,67-,68-,69-,70-,71-,72-,73-/m1/s1
IUPAC Name
N-[(2R,3R,4R,5S,6R)-6-({[(2R,3R,4R,5S,6R)-4-{[(3R)-3-[(5Z)-dodec-5-enoyloxy]decyl]oxy}-3-[(1-hydroxy-3-oxotetradecylidene)amino]-6-(methoxymethyl)-5-(phosphonooxy)oxan-2-yl]oxy}methyl)-5-hydroxy-4-{[(3R)-3-hydroxydecyl]oxy}-2-(phosphonooxy)oxan-3-yl]-3-oxotetradecanimidic acid
SMILES
[H]\C(CCCCCC)=C(/[H])CCCC(=O)O[C@]([H])(CCCCCCC)CCO[C@@]1([H])[C@]([H])(OP(O)(O)=O)[C@@]([H])(COC)O[C@@]([H])(OC[C@@]2([H])O[C@]([H])(OP(O)(O)=O)[C@]([H])(N=C(O)CC(=O)CCCCCCCCCCC)[C@@]([H])(OCC[C@]([H])(O)CCCCCCC)[C@]2([H])O)[C@]1([H])N=C(O)CC(=O)CCCCCCCCCCC

Pharmacology

Indication

Investigated for use/treatment in sepsis and septicemia.

Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UToll-like receptor 4Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
4946357

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00493 mg/mLALOGPS
logP6.33ALOGPS
logP17.73ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)0.5ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area354.98 Å2ChemAxon
Rotatable Bond Count66ChemAxon
Refractivity381.96 m3·mol-1ChemAxon
Polarizability165.64 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transmembrane signaling receptor activity
Specific Function
Cooperates with LY96 and CD14 to mediate the innate immune response to bacterial lipopolysaccharide (LPS). Acts via MYD88, TIRAP and TRAF6, leading to NF-kappa-B activation, cytokine secretion and ...
Gene Name
TLR4
Uniprot ID
O00206
Uniprot Name
Toll-like receptor 4
Molecular Weight
95679.19 Da
References
  1. Mullarkey M, Rose JR, Bristol J, Kawata T, Kimura A, Kobayashi S, Przetak M, Chow J, Gusovsky F, Christ WJ, Rossignol DP: Inhibition of endotoxin response by e5564, a novel Toll-like receptor 4-directed endotoxin antagonist. J Pharmacol Exp Ther. 2003 Mar;304(3):1093-102. [PubMed:12604686]
  2. Becker S, Mundandhara S, Devlin RB, Madden M: Regulation of cytokine production in human alveolar macrophages and airway epithelial cells in response to ambient air pollution particles: further mechanistic studies. Toxicol Appl Pharmacol. 2005 Sep 1;207(2 Suppl):269-75. [PubMed:15993911]

Drug created on March 19, 2008 10:33 / Updated on June 04, 2019 06:24